Highland Park Real Estate

Highland Park Real Estate

Welcome to Highland Park, a hidden gem nestled in the heart of sunny Florida! This vibrant subdivision is more than just a neighborhood; it’s a community brimming with charm, character, and a sense of belonging. Highland Park is known for its picturesque tree-lined streets, beautifully landscaped parks, and a welcoming atmosphere that makes it an ideal place for families, retirees, and everyone in between.

One of the standout features of Highland Park is its commitment to outdoor living. Residents enjoy access to a variety of amenities, including community parks, walking trails, and playgrounds that cater to both children and adults. The community often hosts events that foster neighborly connections, from seasonal festivals to weekend farmers’ markets, making it easy to meet new friends and create lasting memories.

Highland Park is conveniently located near major highways, providing quick access to nearby cities and attractions. Whether you’re looking to explore the vibrant downtown area, indulge in local dining experiences, or take a day trip to Florida’s stunning beaches, you’ll find everything you need just a short drive away.

The real estate options in Highland Park are diverse, featuring charming single-family homes, modern townhouses, and spacious lots for those looking to build their dream home. With a strong sense of community, excellent schools, and a range of recreational activities, Highland Park is not just a place to live; it’s a place to thrive. Discover the beauty and warmth of Highland Park today, and see why so many are proud to call this wonderful subdivision home!

Newest Listings in Highland Park

$749,000
3 Beds 2 Baths Highland Park SubDv. 34239 Zip Code
Welcome to a refined corner-lot home directly across from Arlington Park — one of Sarasota's most beloved neighborhood amenities. With 1,955 sqft of thoughtful living space, three bedrooms with walk-in closets, two updated baths, and a true 2-car garage, this property offers a combination that simply doesn't exist at this price point in the heart of the city. Every detail has been considered for Florida living. A 2022 metal roof with a 50-year warranty, two new Trane HVAC systems, impact-resistant windows, and a new water heater mean lower insurance, lower utilities, and no deferred maintenance. Located in evacuation Zone E and high and dry through every recent storm season, this is the rare home that lets you stop worrying about Florida ownership. Inside, character meets quality: stained solid wood doors, crown molding, hardwood bamboo flooring, a maple stairwell, and warm wooden ceilings. Walk out to a generous screened lanai, private hot tub, and lush tropical landscaping framed by palms, bamboo, and fruit trees. The fully fenced yard provides quiet privacy in a setting most Sarasota buyers only dream about. Step out your front door to Arlington Park's 50-meter lap pool, tennis courts, basketball courts, dog park, and walking trails. Sarasota Memorial Hospital, Southside Village dining, and downtown are all within minutes. Beaches at Siesta Key are a short drive away. Zoned for top-rated Southside Elementary (A-rated). A rare opportunity: turnkey, insurable, and irreplaceable location — directly across from the park.

2690 Temple Street, Sarasota

$415,995
4 Beds 2 Baths Highland Park SubDv. 33770 Zip Code
This beautifully updated block home tucked into one of Pinellas County’s most connected locations. From the moment you arrive, the fresh exterior, oversized driveway, and screened front porch set the tone for a home that feels both inviting and highly functional. Step inside to an open-concept living and dining space that feels anything but cookie-cutter, with LVP flooring throughout, a bold accent wall, stylish ceiling fans, and a designer lantern-lit entryway that leads you right into the heart of the home. At the center of it all is the kitchen — a true showpiece with a large stone-topped island, bar seating, warm pendant lighting, stainless steel appliances, a sliding barn door, and modern farmhouse-style cabinetry. Whether you’re hosting friends, meal prepping for the week, or keeping an eye on the action while you cook, this space is designed to work the way you live. The bedrooms encourage generous natural light, ceiling fans, and comfortable layouts, while the updated bathrooms feature modern vanities and sleek fixtures throughout. A dedicated office/bonus room with its own closet adds valuable flexibility for remote work, a creative studio, or even a fifth bedroom if needed. Step outside and you’ll see where this home truly shines. A fully screened rear porch with a mounted TV opens to a spacious deck, concrete patio with a fire pit area, storage shed, and a fully fenced backyard lined with mature palms and tropical landscaping. This is an outdoor space you’ll actually use — perfect for entertaining, relaxing, or enjoying Florida evenings in your own private retreat. The 2-car garage adds even more versatility with room for vehicles, storage, or a workshop, and the home is EV-ready with an electric vehicle charging setup already in place. Location is the finishing touch that makes this home such a rare find. You’re just one block from the Pinellas Trail, with easy bike access to Dunedin, Clearwater Beach, and St. Petersburg, while Missouri Avenue is steps away with everyday conveniences like Walmart, Aldi, and LA Fitness nearby. Belleair’s waterfront dining and golf courses are minutes away, and you’re just a short drive from the Gulf. High and dry, with no flood zone and no evacuation zone, this is the kind of home that’s hard to find and even harder to leave.

1005 13th Avenue Nw, Largo

$1,725,000
7 Beds 6 Baths Highland Park SubDv. 33770 Zip Code
Price Improvement! This rare 5-unit short-term rental property offers an exceptional opportunity to own a fully established Airbnb-style compound just a short drive to the Gulf beaches and a central hub for nature trails, festivals, and events in downtown Clearwater. ** Listing includes includes Parcel Id 27-29-15-38970-003-0050. Spread across three lots on two parcels, the property includes a spacious main residence along with four individual guest cottages, creating multiple income-producing retreats in one highly desirable Pinellas County location. The property consists of five total units, including four well-appointed 1-bedroom, 1-bath cottages, each approximately 576 square feet, ideal for couples or small families seeking a private Florida getaway. The larger main home spans approximately 1,148 square feet and serves as the centerpiece of the compound with 3 bedrooms and 2 baths, luxury finishes, LVP flooring, a true primary suite with a walk-in closet, a bunk room, and inviting outdoor living spaces. Guests enjoy a side patio for dining plus a screened back porch complete with darts and foosball, creating a resort-style experience. Three of the four cottages share nearly identical layouts for ease of operation and consistent guest appeal, while all units offer generous backyard areas, ample secure parking, and convenient Yale smart lock access. Offered fully furnished and professionally designed, this property is truly turnkey and has been well maintained, while still presenting additional upside, including the potential to add a swimming pool. Laundry is thoughtfully arranged with a washer and dryer inside the main house, plus an additional centrally located utility room with washer and dryer access for cottage guests or cleaning teams. Each unit is separately metered for electric and water, providing added flexibility for future ownership strategies and long-term operational value. Adding to the uniqueness of the offering is the street-to-street frontage between 15th Avenue Northwest and 16th Avenue Northwest, along with mixed-use zoning that may provide future redevelopment or expansion potential as the surrounding area continues to grow. Surrounded by tropical landscaping with palm and orange trees, and located minutes from Clearwater, Belleair, and Indian Rocks Beach, yet positioned in Airbnb-friendly Largo, this is a truly rare chance to operate a well-performing short-term rental compound in one of Florida’s most in-demand coastal markets.

1500 Clearwater Largo Road N, Largo

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